The present invention relates to novel substituted (4-bromopyrazol-3-yl)benzazoles of the formula I 
where:
R1 is hydrogen, C1-C4-alkyl or C1-C4-haloalkyl;
R2 is cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl or C1-C4-haloalkylsulfonyl;
R4 is hydrogen or halogen;
R5 is hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 or xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 which may be attached to xcex1 via the nitrogen, oxygen or sulfur;
X is a chemical bond, oxygen, sulfur, xe2x80x94S(O)xe2x80x94, xe2x80x94SO2xe2x80x94, xe2x80x94NHxe2x80x94 or xe2x80x94N(R7)xe2x80x94;
R6, R7 independently of one another are each C1-C6-alkyl, C1-C6-haloalkyl, cyano-C1-C4-alkyl, hydroxy-C1-C4-alkyl, C3-C6-alkenyl, cyano-C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, cyano-C3-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C3-C4-alkenyloxy-C1-C4-alkyl, C3-C4-alkynyloxy-C1-C4-alkyl, C3-C8-cycloalkyloxy-C1-C4-alkyl, amino-C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, di(C1-C4-alkyl)amino-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-haloalkylthio-C1-C4-alkyl, C3-C4-alkenylthio-C1-C4-alkyl, C3-C4-alkynylthio-C1-C4-alkyl, C1-C4-alkyl sulfinyl-C1-C4-alkyl, C1-C4-haloalkylsulfinyl-C1-C4-alkyl, C3-C4-alkenylsulfinyl-C1-C4-alkyl, C3-C4-alkynylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, C1-C4-haloalkylsulfonyl-C1-C4-alkyl, C3-C4-alkenyl sulfonyl-C1-C4-alkyl, C3-C4-alkynylsulfonyl-C1-C4-alkyl, hydroxycarbonyl-C1-C4-alkyl, (C1-C4-alkoxy)carbonyl-C1-C4-alkyl, which may carry a cyano or (C1-C4-alkoxy)carbonyl group, (C1-C4-alkylthio)carbonyl-C1-C4-alkyl, aminocarbonyl-C1-C4-alkyl, C1-C4-alkylaminocarbonyl-C1-C4-alkyl, di(C1-C4-alkyl)aminocarbonyl-C1-C4-alkyl, di(C1-C4-alkyl)-phosphonyl-C1-C4-alkyl, (C1-C4-alkoxy)imino-C1-C4-alkyl, (C3-C4-alkenyloxy)imino-C1-C4-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, 3- to 7-membered heterocyclyl or heterocyclyl-C1-C4-alkyl, where each cycloalkyl and each heterocyclyl ring may contain a carbonyl or thiocarbonyl ring member, and where each cycloalkyl, phenyl and heterocyclyl ring may be unsubstituted or may carry from one to four substituents, in each case selected from the group consisting of cyano, nitro, amino, hydroxyl, carboxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, (C1-C4-alkoxy)carbonyl, (C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, (C1-C4-alkyl)carbonyloxy, (C1-C4-haloalkyl)carbonyloxy and di(C1-C4-alkyl)amino;
if x is a chemical bond, oxygen, sulfur, xe2x80x94NHxe2x80x94 or xe2x80x94N(R7)xe2x80x94, R6 may also be (C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, (C1-C4-alkoxy)carbonyl, C1-C4-alkylsulfonyl or C1-C4-haloalkylsulfonyl;
if X is a chemical bond, R6 may furthermore be hydrogen, cyano, mercapto, amino, halogen, xe2x80x94CH2xe2x80x94CH(halogen)-R8, xe2x80x94CHxe2x95x90CHxe2x80x94R8 or xe2x80x94CHxe2x95x90C(halogen)-R8, where R8 is hydroxycarbonyl, (C1-C4-alkoxy)carbonyl, (C1-C4-alkylthio)carbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)aminocarbonyl or di(C1-C4-alkyl)phosphonyl;
or R6 and R7 together are a 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain which may in each case be unsubstituted or may carry from 1 to 4 C1-C4-alkyl groups or one or two (C1-C4-alkoxy)carbonyl groups,
and the agriculturally useful salts of these compounds I.
Furthermore, the invention relates to
the use of the compounds I as herbicides and/or for the desiccation and/or defoliation of plants,
herbicidal compositions and compositions for the desiccation and/or defoliation of plants which comprise the compounds I as active ingredients,
processes for preparing the compounds I and herbicidal compositions and compositions for the desiccation/defoliation of plants using the compounds I,
methods for controlling undesirable vegetation and for the desiccation and/or defoliation of plants using the compounds I, and also
novel intermediates of the formulae Va and Vb.
The present (4-bromopyrazol-3-yl)benzazoles I are covered by the general formula of active compounds which form part of the subject matter of the earlier application DE-A 19 652 240.
It is an object of the present invention to provide novel herbicidally active pyrazole compounds which allow better selective control of undesirable plants than the compounds of the prior art. It is a further object to provide novel compounds which have a desiccant/defoliant action.
We have found that these objects are achieved by the present substituted (4-bromopyrazol-3-yl)benzazoles of the formula I.
Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Furthermore, we have found that the compounds I are also suitable for the desiccation/defoliation of parts of plants, suitable plants being crop plants such as cotton, potatoes, oil seed rape, sunflower, soybean or field beans, in particular cotton. Thus, we have found compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for the desiccation and/or defoliation of plants using the compounds I.
Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they exist in the form of enantiomer or diastereomer mixtures. For compounds I having at least one olefinic radical, E/Z isomers may also be possible. The invention provides both the pure enantiomers or diastereomers and also mixtures thereof.
The organic moieties mentioned in the definition of the substituents R1, R2 and R5 to R8 or as radicals on cycloalkyl, phenyl or heterocyclic rings arexe2x80x94like the term halogenxe2x80x94collective terms for individual listings of the individual group members. All carbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl, oxyalkyl, aminoalkyl, oxycarbonylalkyl, aminocarbonylalkyl, phosphonylalkyl, oxyaminoalkyl, phenylalkyl, heterocyclylalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl and cyanoalkynyl moieties, can be straight-chain or branched. Halogenated substituents preferably carry from 1 to 5 identical or different halogen atoms. The term halogen represents in each case fluorine, chlorine, bromine or iodine.
Other examples of meanings are:
C1-C4-alkyl: CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, 1-methylpropyl, 2-methylpropyl or C(CH3)3;
C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, CH2F, CHF2, CF3, CH2Cl, CH(Cl)2, C(Cl)3, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, C2F5, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH2xe2x80x94C2F5, CF2xe2x80x94C2F5, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;
C1-C6-alkyl: C1-C4-alkyl as mentioned above, and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably
CH3, C2H5, CH2xe2x80x94C2H5, CH(CH3)2, n-butyl, C(CH3)3, n-pentyl or n-hexyl;
C1-C6-haloalkyl: a C1-C6-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, one of the radicals mentioned under C1-C4-haloalkyl or 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, n-C5F11, 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl, 6,6,6-trichloro-1-hexyl or dodecafluorohexyl;
cyano-C1-C4-alkyl: CH2CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 3-cyanobut-2-yl, 4-cyanobut-2-yl, 1-(CH2CN)eth-1-yl, 1-(CH2CN)-1-(CH3)-eth-1-yl or 1-(CH2CN)prop-1-yl;
hydroxy-C1-C4-alkyl: CH2OH, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxyprop-1-yl, 2-hydroxyprop-1-yl, 3-hydroxyprop-1-yl, 1-hydroxybut-1-yl, 2-hydroxybut-1-yl, 3-hydroxybut-1-yl, 4-hydroxybut-1-yl, 1-hydroxybut-2-yl, 2-hydroxybut-2-yl, 3-hydroxybut-2-yl, 4-hydroxybut-2-yl, 1-(CH2OH)eth-1-yl, 1-(CH2OH)-1-(CH3)-eth-1-yl or 1-(CH2OH)prop-1-yl;
amino-C1-C4-alkyl: CH2NH2, 1-aminoethyl, 2-aminoethyl, 1-aminoprop-1-yl, 2-aminoprop-1-yl, 3-aminoprop-1-yl, 1-amino-but-1-yl, 2-aminobut-1-yl, 3-aminobut-1-yl, 4-aminobut-1-yl, 1-aminobut-2-yl, 2-aminobut-2-yl, 3-aminobut-2-yl, 4-amino-but-2-yl, 1-(CH2NH2)eth-1-yl, 1-(CH2NH2)-1-(CH3)-eth-1-yl or 1-(CH2NH2)prop-1-yl;
hydroxycarbonyl-C1-C4-alkyl: CH2COOH, 1-(COOH)ethyl, 2-(COOH)ethyl, 1-(COOH)prop-1-yl, 2-(COOH)prop-1-yl, 3-(COOH)prop-1-yl, 1-(COOH)but-1-yl, 2-(COOH)but-1-yl, 3-(COOH)but-1-yl, 4-(COOH)but-1-yl, 1-(COOH)but-2-yl, 2-(COOH)but-2-yl, 3-(COOH)but-2-yl, 4-(COOH)but-2-yl, 1-(CH2COOH)eth-1-yl, 1-(CH2COOH)-1-(CH3)eth-1-yl or 1-(CH2COOH)prop-1-yl;
aminocarbonyl-C1-C4-alkyl: CH2CONH2, 1-(CONH2)ethyl, 2-(CONH2)ethyl, 1-(CONH2)prop-1-yl, 2-(CONH2)prop-1-yl, 3-(CONH2)prop-1-yl, 1-(CONH2)but-1-yl, 2-(CONH2)but-1-yl, 3-(CONH2)but-1-yl, 4-(CONH2)but-1-yl, 1-(CONH2)but-2-yl, 2-(CONH2)but-2-yl, 3-(CONH2)but-2-yl, 4-(CONH2)but-2-yl, 1-(CH2CONH2)eth-1-yl, 1-(CH2CONH2)-1-(CH3)eth-1-yl or 1-(CH2CONH2)prop-1-yl;
phenyl-C1-C4-alkyl: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1-(benzyl)eth-1-yl, 1-(benzyl)-1-(methyl)eth-1-yl or 1-(benzyl)prop-1-yl, preferably benzyl or 2-phenylethyl;
heterocyclyl-C1-C4-alkyl: heterocyclylmethyl, 1-heterocyclylethyl, 2-heterocyclylethyl, 1-heterocyclylprop-1-yl, 2-heterocyclylprop-1-yl, 3-heterocyclylprop-1-yl, 1-heterocyclylbut-1-yl, 2-heterocyclylbut-1-yl, 3-heterocyclylbut-1-yl, 4-heterocyclylbut-1-yl, 1-heterocyclylbut-2-yl, 2-heterocyclylbut-2-yl, 3-heterocyclylbut-2-yl, 3-heterocyclylbut-2-yl, 4-heterocyclylbut-2-yl, 1-(heterocyclylmethyl)eth-1-yl, 1-(heterocyclylmethyl)-1-(methyl)eth-1-yl or 1-(heterocyclylmethyl)prop-1-yl, preferably heterocyclylmethyl or 2-heterocyclylethyl;
C1-C4-alkoxy: OCH3, OC2H5, OCH2xe2x80x94C2H5, OCH(CH3)2, n-butoxy, OCH(CH3)xe2x80x94C2H5, OCH2xe2x80x94CH(CH3)2 or C(CH3)3, preferably OCH3, OC2H5 or OCH(CH3)2;
C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCH(Cl)2, OC(Cl)3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2xe2x80x94C2F5, OCF2xe2x80x94C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, preferably OCHF2, OCF3, dichlorofluoromethoxy, chlorodifluoromethoxy or 2,2,2-trifluoroethoxy;
C1-C4-alkylthio: SCH3, SC2H5, SCH2xe2x80x94C2H5, SCH(CH3)2, n-butylthio, 1-methylpropylthio, SCH2xe2x80x94CH(CH3)2 or SC(CH3)3, preferably SCH3 or SC2H5;
C1-C4-haloalkylthio: a C1-C4-alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, SCH2F, SCHF2, SCF3, SCH2Cl, SCH(Cl)2, SC(Cl)3, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, SC2F5, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH2xe2x80x94C2F5, SCF2xe2x80x94C2F5, 1-(CH2F)-2-fluoroethylthio, 1-(CH2Cl)-2-chloroethylthio, 1-(CH2Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or SCF2xe2x80x94CF2xe2x80x94C2F5, preferably SCHF2, SCF3, dichlorofluoromethylthio, chlorodifluoromethylthio or 2,2,2-trifluoroethylthio;
C1-C4-alkoxy-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-alkoxyxe2x80x94as mentioned abovexe2x80x94, i.e., for example, CH2xe2x80x94OCH3, CH2xe2x80x94OC2H5, n-propoxymethyl, CH2xe2x80x94OCH(Ch3)2, n-butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CH2xe2x80x94OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl, preferably CH2xe2x80x94OCH3, CH2xe2x80x94OC2H5, 2-(OCH3)ethyl or 2-(OC2H5)ethyl;
C1-C4-haloalkoxy-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-haloalkoxy as mentioned above, i.e., for example, 2-(OCHF2)ethyl, 2-(OCF3)ethyl or 2-(OC2F5)ethyl;
C1-C4-alkylthio-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-alkylthioxe2x80x94as mentioned above, i.e.,xe2x80x94for example, CH2xe2x80x94SCH3, CH2xe2x80x94SC2H5, n-propylthiomethyl, CH2xe2x80x94SCH(CH3)2, n-butylthiomethyl, (1-methylpropylthio)methyl, (2-methylpropylthio)methyl, CH2xe2x80x94SC(CH3)3, 2-((methylthio)ethyl, 2-(ethylthio)ethyl, 2-(n-propylthio)ethyl, 2-(1-methylethylthio)ethyl, 2-(n-butylthio)ethyl, 2-(1-methylpropylthio)ethyl, 2-(2-methylpropylthio)ethyl, 2-(1,1-dimethylethylthio)ethyl, 2-(methylthio)propyl, 2-(ethylthio)propyl, 2-(n-propylthio)propyl, 2-(1-methylethylthio )propyl, 2-(n-butylthio )propyl, 2-(1-methylpropylthio)propyl, 2-(2-methylpropylthio)propyl, 2-(1,1-dimethylethylthio)propyl, 3-(methylthio)propyl, 3-(ethylthio)propyl, 3-(n-propylthio)propyl, 3-(1-methylethylthio)propyl, 3-(n-butylthio)propyl, 3-(1-methylpropylthio)propyl, 3-(2-methylpropylthio)propyl, 3-(1,1-dimethylethylthio)propyl, 2-(methylthio)butyl, 2-2-(ethylthio)butyl, 2-(n-propylthio)butyl, 2-(1-methylethylthio)butyl, 2-(n-butylthio)butyl, 2-(1-methylpropylthio)butyl, 2-(2-methylpropylthio)butyl, 2-(1,1-dimethylethylthio)butyl, 3-(methylthio)butyl, 3-(ethylthio)butyl, 3-(n-propylthio)butyl, 3-(1-methylethylthio)butyl, 3-(n-butylthio)butyl, 3-(1-methylpropylthio)butyl, 3-(2-methylpropylthio)butyl, 3-(1,1-dimethylethylthio)butyl, 4-(methylthio)butyl, 4-(ethylthio)butyl, 4-(n-propylthio)butyl, 4-(1-methylethylthio)butyl, 4-(n-butylthio)butyl, 4-(1-methylpropylthio)butyl, 4-(2-methylpropylthio)butyl or 4-(1,1-dimethylethylthio)butyl, preferably CH2xe2x80x94SCH3, CH2xe2x80x94SC2H5, 2-(SCH3)ethyl or 2-(SC2H5)ethyl;
C1-C4-haloalkylthio-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-haloalkylthio as mentioned above, i.e., for example, 2-(SCHF2)ethyl, 2-(SCF3)ethyl or 2-(SC2F5)ethyl;
(C1-C4-alkoxy)imino-C1-C4-alkyl: C1-C4-alkyl which is substituted by (C1-C4-alkoxy)imino such asxe2x95x90Nxe2x80x94CH3, xe2x95x90Nxe2x80x94C2H5, xe2x95x90NCH2xe2x80x94C2H5, xe2x95x90Nxe2x80x94CH(CH3)2, xe2x95x90NCH2xe2x80x94CH2xe2x80x94C2H5, xe2x95x90NCH(CH3)xe2x80x94C2H5, xe2x95x90NCH2xe2x80x94CH(CH3)2 or =Nxe2x80x94C(CH3)3, i.e., for example, Chxe2x95x90Nxe2x80x94CH3, CHxe2x95x90Nxe2x80x94C2H5, CH2xe2x80x94CHxe2x95x90Nxe2x80x94CH3 or CH2xe2x80x94CHxe2x95x90Nxe2x80x94C2H5;
(C1-C4-alkyl)carbonyl: COxe2x80x94CH3, COxe2x80x94C2H5, COxe2x80x94CH2xe2x80x94C2H5, COxe2x80x94CH(CH3)2, n-butylcarbonyl, COxe2x80x94CH(CH3)xe2x80x94C2H5, COxe2x80x94CH2xe2x80x94CH(CH3)2 or COxe2x80x94C(CH3)3, preferably COxe2x80x94CH3 or COxe2x80x94C2H5;
(C1-C4-haloalkyl)carbonyl: a (C1-C4-alkyl)carbonyl radicalxe2x80x94as mentioned abovexe2x80x94which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, COxe2x80x94CH2F, COxe2x80x94CHF2, COxe2x80x94CF3, COxe2x80x94CH2Cl, COxe2x80x94CH(C1)2, COxe2x80x94C(Cl)3, chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl, chlorodifluoromethylcarbonyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, COxe2x80x94C2F5, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, COxe2x80x94CH2xe2x80x94C2F5, COxe2x80x94CF2xe2x80x94C2F5, 1-(CH2F)-2-fluoroethylcarbonyl, 1-(CH2Cl)-2-chloroethylcarbonyl, 1-(CH2Br)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl, preferably COxe2x80x94CF3 COxe2x80x94CH2Cl or 2,2,2-trifluoroethylcarbonyl;
(C1-C4-alkyl)carbonyloxy: Oxe2x80x94COxe2x80x94CH3, Oxe2x80x94COxe2x80x94C2H5, Oxe2x80x94COxe2x80x94CH2xe2x80x94C2H5, Oxe2x80x94COxe2x80x94CH(CH3)2, Oxe2x80x94COxe2x80x94CH2xe2x80x94CH2xe2x80x94C2H5, Oxe2x80x94COxe2x80x94CH(CH3)xe2x80x94C2H5, Oxe2x80x94COxe2x80x94CH2xe2x80x94CH(CH3)2 or Oxe2x80x94COxe2x80x94C(CH3)3, preferably Oxe2x80x94COxe2x80x94CH3 or Oxe2x80x94COxe2x80x94C2H5;
(C1-C4-haloalkyl)carbonyloxy: a (C1-C4-alkyl)carbonyl radicalxe2x80x94as mentioned abovexe2x80x94which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, Oxe2x80x94COxe2x80x94CH2F, Oxe2x80x94COxe2x80x94CHF2, Oxe2x80x94COxe2x80x94CF3, Oxe2x80x94COxe2x80x94CH2Cl, Oxe2x80x94COxe2x80x94CH(Cl)2, Oxe2x80x94COxe2x80x94C(Cl)3, chlorofluoromethylcarbonyloxy, dichlorofluoromethylcarbonyloxy, chlorodifluoromethylcarbonyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2,2-difluoroethylcarbonyloxy, 2,2-dichloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, Oxe2x80x94COxe2x80x94C2F5, 2-fluoropropylcarbonyloxy, 3-fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy, 2,3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 3,3,3-trifluoropropylcarbonyloxy, 3,3,3-trichloropropylcarbonyloxy, Oxe2x80x94COxe2x80x94CH2xe2x80x94C2F5, Oxe2x80x94COxe2x80x94CF2xe2x80x94C2F5, 1-(CH2F)-2-fluoroethylcarbonyloxy, 1-(CH2Cl)-2-chloroethylcarbonyloxy, 1-(CH2Br)-2-bromoethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutylcarbonyloxy or nonafluorobutylcarbonyloxy, preferably Oxe2x80x94COxe2x80x94CF3, Oxe2x80x94COxe2x80x94CH2Cl or 2,2,2-trifluoroethylcarbonyloxy;
(C1-C4-alkoxy)carbonyl: COxe2x80x94OCH3, COxe2x80x94OC2H5, n-propoxycarbonyl, COxe2x80x94OCH(CH3)2, n-butoxycarbonyl, COxe2x80x94OCH(CH3)xe2x80x94C2H5, COxe2x80x94OCH2xe2x80x94CH(CH3)2 or COxe2x80x94OC(CH3)3, preferably COxe2x80x94OCH3 or COxe2x80x94OC2H5;
(C1-C4-alkoxy)carbonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by (C1-C4-alkoxy)carbonylxe2x80x94as mentioned abovexe2x80x94, i.e., for example, CH2xe2x80x94COxe2x80x94OCH3, CH2xe2x80x94COxe2x80x94OC2H5, n-propoxycarbonyl-methyl, CH2xe2x80x94COxe2x80x94OCH(CH3)2, n-butoxycarbonylmethyl, CH2xe2x80x94COxe2x80x94OCH(CH3)xe2x80x94C2H5, CH2xe2x80x94COxe2x80x94OCH2xe2x80x94CH(CH3)2, CH2xe2x80x94COxe2x80x94OC(CH3)3, 1-(methoxycarbonyl)ethyl, 1-(ethoxycarbonyl)ethyl, 1-(n-propoxycarbonyl)ethyl, 1-(1-methylethoxycarbonyl)ethyl, 1-(n-butoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(n-propoxycarbonyl)ethyl, 2-(1-methylethoxycarbonyl)ethyl, 2-(n-butoxycarbonyl)ethyl, 2-(1-methylpropoxycarbonyl)ethyl, 2-(2-methylpropoxycarbonyl)-ethyl, 2-(1,1-dimethylethoxycarbonyl)ethyl, 2-(methoxycarbonyl)propyl, 2-(ethoxycarbonyl)propyl, 2-(n-propoxycarbonyl)propyl, 2-(1-methylethoxycarbonyl)propyl, 2-(n-butoxycarbonyl)propyl, 2-(1-methylpropoxycarbonyl)propyl, 2-(2-methylpropoxycarbonyl)propyl, 2-(1,1-dimethylethoxycarbonyl)propyl, 3-(methoxycarbonyl)propyl, 3-(ethoxycarbonyl)propyl, 3-(n-propoxycarbonyl)propyl, 3-(1-methylethoxycarbonyl)propyl, 3-(n-butoxycarbonyl)propyl, 3-(1-methylpropoxycarbonyl)propyl, 3-(2-methylpropoxycarbonyl)propyl, 3-(1,1-dimethylethoxycarbonyl)propyl, 2-(methoxycarbonyl)butyl, 2-(ethoxycarbonyl)butyl, 2-(n-propoxycarbonyl)butyl, 2-(1-methylethoxycarbonyl)butyl, 2-(n-butoxycarbonyl)butyl, 2-(1-methylpropoxycarbonyl)butyl, 2-(2-methylpropoxycarbonyl)-butyl, 2-(1,1-dimethylethoxycarbonyl)butyl, 3-(methoxycarbonyl)butyl, 3-(ethoxycarbonyl)butyl, 3-(n-propoxycarbonyl)butyl, 3-(1-methylethoxycarbonyl)butyl, 3-(n-butoxycarbonyl)butyl, 3-(1-methylpropoxycarbonyl)butyl, 3-(2-methylpropoxycarbonyl)butyl, 3-(1,1-dimethylethoxycarbonyl)butyl, 4-(methoxycarbonyl)butyl, 4-(ethoxycarbonyl)butyl, 4-(n-propoxycarbonyl)butyl, 4-(1-methylethoxycarbonyl)butyl, 4-(n-butoxycarbonyl)butyl, 4-(1-methylpropoxycarbonyl)butyl, 4-(2-methylpropoxycarbonyl)-butyl or 4-(1,1-dimethylethoxycarbonyl)butyl, preferably CH2xe2x80x94COxe2x80x94OCH3, CH2xe2x80x94COxe2x80x94OC2H5, 1-(methoxycarbonyl)ethyl or 1-(ethoxycarbonyl)ethyl;
(C1-C4-alkylthio)carbonyl: COxe2x80x94SCH3, COxe2x80x94SC2H5, COxe2x80x94SCH2xe2x80x94C2H5, COxe2x80x94SCH(CH3)2, COxe2x80x94SCH2CH2xe2x80x94C2H5, COxe2x80x94SCH(CH3)xe2x80x94C2H5, COxe2x80x94SCH2xe2x80x94CH(CH3)2 or COxe2x80x94SC(CH3)3, preferably COxe2x80x94SCH3 or COxe2x80x94SC2H5;
(C1-C4-alkylthio)carbonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by (C1-C4-alkylthio)carbonylxe2x80x94as mentioned abovexe2x80x94, i.e., for example, CH2xe2x80x94COxe2x80x94SCH3, CH2xe2x80x94COxe2x80x94SC2H5, CH2xe2x80x94COxe2x80x94SCHsxe2x80x94H5, CH2xe2x80x94COxe2x80x94SCH(CH3)2, CH2xe2x80x94COxe2x80x94SCH2CH2xe2x80x94C2H5, CH2xe2x80x94COxe2x80x94SCH(CH3)xe2x80x94C2H5, CH2xe2x80x94COxe2x80x94SCH2xe2x80x94CH(CH3)2, CH2xe2x80x94COxe2x80x94SC(CH3)3, 1-(COxe2x80x94SCH3)ethyl, 1-(COxe2x80x94SC2H5)ethyl, 1-(COxe2x80x94SCH2xe2x80x94C2H5)ethyl, 1-[COxe2x80x94SCH(CH3)2]ethyl, 1-(COxe2x80x94SCH2CH2xe2x80x94C2H5)ethyl, 1-[COxe2x80x94SCH(CH3)xe2x80x94C2H5]ethyl, 1-[COxe2x80x94SCH2xe2x80x94CH(CH3)2]ethyl, 1-[COxe2x80x94SC (CH3)3]ethyl, 2-(COxe2x80x94SCH3)ethyl, 2-(COxe2x80x94SC2H5)ethyl, 2-(COxe2x80x94SCH2xe2x80x94C2H5)ethyl, 2-[COxe2x80x94SCH(CH3)2]ethyl, 2-(COxe2x80x94SCH2CH2xe2x80x94C2H5)ethyl, 2-[COxe2x80x94SCH(CH3)xe2x80x94C2H5]ethyl, 2-[COxe2x80x94SCH2xe2x80x94CH(CH3)2]ethyl, 2-[COxe2x80x94SC(CH3)3]ethyl, 2-(COxe2x80x94SCH3)-propyl, 2-(COxe2x80x94SC2H5)propyl, 2-(COxe2x80x94SCH2xe2x80x94C2H5)propyl, 2-[COxe2x80x94SCH(CH3)2]propyl, 2-(COxe2x80x94SCH2CH2xe2x80x94C2H5)propyl, 2-[COxe2x80x94SCH(CH3)xe2x80x94C2H5]propyl, 2-[COxe2x80x94SCH2xe2x80x94CH(CH3)2]propyl, 2-[COxe2x80x94SC(CH3)3]propyl, 3-(COxe2x80x94SCH3)propyl, 3-(COxe2x80x94SC2H5)propyl, 3-(COxe2x80x94SCH2xe2x80x94C2H5)propyl, 3-[COxe2x80x94SCH(CH3)2]propyl, 3-(COxe2x80x94SCH2CH2xe2x80x94C2H5)propyl, 3-[COxe2x80x94SCH(CH3)xe2x80x94C2H5]propyl, 3-[COxe2x80x94SCH2xe2x80x94CH(CH3)2]propyl, 3-[COxe2x80x94SC(CH3)3]propyl, 2-(COxe2x80x94SCH3)butyl, 2-(COxe2x80x94SC2H5)butyl, 2-(COxe2x80x94SCH2xe2x80x94C2H5)butyl, 2-[COxe2x80x94SCH(CH3)2]butyl, 2-(COxe2x80x94SCH2CH2xe2x80x94C2H5)butyl, 2-[COxe2x80x94SCH(CH3)xe2x80x94C2H5]butyl, 2-[COxe2x80x94SCH2xe2x80x94CH(CH3)2]butyl, 2-[COxe2x80x94SC(CH3)3]butyl, 3-(COxe2x80x94SCH3)butyl, 3-(COxe2x80x94SC2H5)butyl, 3-(COxe2x80x94SCH2xe2x80x94C2H5)butyl, 3-[COxe2x80x94SCH(CH3)2]butyl, 3-(COxe2x80x94SCH2CH2xe2x80x94C2H5)butyl, 3-[COxe2x80x94SCH(CH3)xe2x80x94C2H5]butyl, 3-[COxe2x80x94SCH2xe2x80x94CH(CH3)2]butyl, 3-[COxe2x80x94SC(CH3)3]butyl, 4-(COxe2x80x94SCH3)-butyl, 4-(COxe2x80x94SC2H5)butyl, 4-(COxe2x80x94SCH2xe2x80x94C2H5)butyl, 4-[COxe2x80x94SCH(CH3)2]butyl, 4-(COxe2x80x94SCH2CH2xe2x80x94C2H5)butyl, 4-[COxe2x80x94SCH(CH3)xe2x80x94C2H5]butyl, 4-[COxe2x80x94SCH2xe2x80x94CH(CH3)2]butyl or 4-[COxe2x80x94SC(CH3)3]butyl, preferably CH2xe2x80x94COxe2x80x94SCH3, CH2xe2x80x94COxe2x80x94SC2H5, 1-(COxe2x80x94SCH3)ethyl or 1-(COxe2x80x94SC2H5)ethyl;
C1-C4-alkylsulfinyl: SOxe2x80x94CH3, SOxe2x80x94C2H5, SOxe2x80x94CH2xe2x80x94C2H5, SOxe2x80x94CH(CH3)2, n-butylsulfinyl, SOxe2x80x94CH(CH3)xe2x80x94C2H5, SOxe2x80x94CH2xe2x80x94CH(CH3)2 or SOxe2x80x94C(CH3)3, preferably SOxe2x80x94CH3 or SOxe2x80x94C2H5;
C1-C4-haloalkylsulfinyl: a C1-C4-alkylsulfinyl radicalxe2x80x94as mentioned abovexe2x80x94which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e, for example, SOxe2x80x94CH2F, SOxe2x80x94CHF2, SOxe2x80x94CF3, SOxe2x80x94CH2Cl, SOxe2x80x94CH(Cl)2, SOxe2x80x94C(Cl)3, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, SOxe2x80x94C2F5, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, SOxe2x80x94CH2xe2x80x94C2F5, SOxe2x80x94CF2xe2x80x94C2F5, 1-(CH2F)-2-fluoroethylsulfinyl, 1-(CH2Cl)-2-chloroethylsulfinyl, 1-(CH2Br)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl, preferably SOxe2x80x94CF3, SOxe2x80x94CH2Cl or 2,2,2-trifluoroethylsulfinyl;
C1-C4-alkylsulfinyl-C1-C4-alkyl: C1-C4-alkyl which is subsituted by C1-C4-alkylsulfinyl as mentioned above, i.e., for example, CH2SOCH3, CH2SOC2H5, n-propylsulfinylmethyl, CH2SOCH(CH3)2, n-butylsulfinylmethyl, (1-methylpropylsulfinyl)methyl, (2-methylpropylsulfinyl)methyl, (1,1-dimethylethylsulfinyl)-methyl, 2-methylsulfinylethyl, 2-ethylsulfinylethyl, 2-(n-propylsulfinyl)ethyl, 2-(1-methylethylsulfinyl)ethyl, 2-(n-butylsulfinyl)ethyl, 2-(1-methylpropylsulfinyl)ethyl, 2-(2-methylpropylsulfinyl)ethyl, 2-(1,1-dimethylethylsulfinyl)ethyl, 2-(SOCH3)propyl, 3-(SOCH3)propyl, 2-(SOC2H5)propyl, 3-(SOC2H5)propyl, 3-(propylsulfinyl)propyl, 3-(butylsulfinyl)propyl, 4-(SOCH3)butyl, 4-(SOC2H5)butyl, 4-(n-propylsulfinyl)butyl or 4-(n-butylsulfinyl)butyl, in particular 2-(SOCH3)ethyl;
C1-C4-haloalkylsulfinyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-haloalkylsulfinyl as mentioned above, i.e, for example, 2-(2,2,2-trifluoroethylsulfinyl)ethyl;
C1-C4-alkylsulfonyl: SO2xe2x80x94CH3, SO2xe2x80x94C2H5, SO2xe2x80x94CH2xe2x80x94C2H5, SO2xe2x80x94CH(CH3)2, n-butylsulfonyl, SO2xe2x80x94CH(CH3)xe2x80x94C2H5, SO2xe2x80x94CH2xe2x80x94CH(CH3)2 or SO2xe2x80x94C(CH3)3, preferably SO2xe2x80x94CH3 or SO2xe2x80x94C2H5;
C1-C4-haloalkylsulfonyl: a C1-C4-alkylsulfonyl radicalxe2x80x94as mentioned abovexe2x80x94which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, SO2xe2x80x94CH2F, SO2xe2x80x94CHF2, SO2xe2x80x94CF3, SO2xe2x80x94CH2Cl, SO2xe2x80x94CH(Cl)2, SO2xe2x80x94C(Cl)3, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, SO2xe2x80x94C2F5, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, SO2xe2x80x94CH2xe2x80x94C2F5, SO2xe2x80x94CF2xe2x80x94C2F5, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl, preferably SO2xe2x80x94CH2Cl, SO2xe2x80x94CF3 or 2,2,2-trifluoroethylsulfonyl;
C1-C4-alkylsulfonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by xe2x80x94C1xe2x80x94C4-alkylsulfonyl as mentioned above, i.e., for example, CH2SO2xe2x80x94CH3, CH2SO2xe2x80x94C2H5, CH2SO2xe2x80x94CH2xe2x80x94C2H5, CH2SO2xe2x80x94CH(CH3)2, CH2SO2xe2x80x94CH2CH2xe2x80x94C2H5, (1-methylpropylsulfonyl)methyl, (2-methylpropylsulfonyl)methyl, CH2SO2xe2x80x94C(CH3)3, CH(CH3)SO2xe2x80x94CH3, CH(CH3)SO2xe2x80x94C2H5, CH2CH2SO2xe2x80x94CH3, CH2CH2SO2xe2x80x94C2H5, CH2CH2SO2xe2x80x94CH2xe2x80x94C2H5, CH2CH2SO2xe2x80x94CH (CH3)2, CH2CH2SO2xe2x80x94CH2CH2xe2x80x94C2H5, 2-(1-methylpropylsulfonyl)ethyl, 2-(2-methylpropylsulfonyl)ethyl, CH2CH2SO2xe2x80x94C(CH3)3, 2-(SO2xe2x80x94CH3)propyl, 2-(SO2xe2x80x94C2H5)propyl, 2-(SO2CH2xe2x80x94C2H5)propyl, 2-[SO2xe2x80x94CH(CH3)2]propyl, 2-(SO2xe2x80x94CH2CH2xe2x80x94C2H5)propyl, 2-(1-methylpropylsulfonyl)propyl, 2-(2-methylpropylsulfonyl)propyl, 2-[SO2xe2x80x94C(CH3)3]propyl, 3-(SO2xe2x80x94CH3)propyl, 3-(SO2xe2x80x94C2H5)propyl, 3-(SO2CH2xe2x80x94C2H5)propyl, 3-[SO2xe2x80x94CH(CH3)2]propyl, 3-(SO2xe2x80x94CH2CH2xe2x80x94C2H5)propyl, 3-(1-methylpropylsulfonyl)propyl, 3-(2-methylpropylsulfonyl)propyl, 3-[SO2xe2x80x94C(CH3)3]propyl, 2-(SO2xe2x80x94CH3)butyl, 2-(SO2xe2x80x94C2H5)butyl, 2-(SO2CH2xe2x80x94C2H5)butyl, 2-[SO2xe2x80x94CH(CH3)2]butyl, 2-(SO2xe2x80x94CH2CH2xe2x80x94C2H5)butyl, 2-(1-methylpropylsulfonyl)butyl, 2-(2-methylpropylsulfonyl)butyl, 2-[SO2xe2x80x94C(CH3)3]butyl, 3-(SO2xe2x80x94CH3)butyl, 3-(SO2xe2x80x94C2H5)butyl, 3-(SO2xe2x80x94CH2xe2x80x94C2H5) 3-[SO2xe2x80x94CH(CH3)2]butyl, 3-(SO2xe2x80x94CH2CH2xe2x80x94C2H5)butyl, 3-(1-methylpropylsulfonyl)butyl, 3-(2-methylpropylsulfonyl)butyl, 3-[SO2xe2x80x94C(CH3)3]butyl, 4-(SO2xe2x80x94CH3)butyl, 4-(SO2xe2x80x94C2H5)butyl, 4-(SO2xe2x80x94CH2xe2x80x94C2H5) 4-[SO2xe2x80x94CH(CH3)2]butyl, 4-(SO2xe2x80x94CH2CH2xe2x80x94C2H5)butyl, 4-(1-methylpropylsulfonyl)butyl, 4-(2-methylpropylsulfonyl)butyl or 4-[SO2xe2x80x94C(CH3)3]butyl, in particular CH2CH2SO2xe2x80x94CH3 or CH2CH2SO2xe2x80x94C2H5;
C1-C4-haloalkylsulfonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-haloalkylsulfonyl as mentioned above, i.e., for example, 2-(2,2,2-trifluoroethylsulfonyl)ethyl;
C1-C4-alkylamino-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-alkylamino such as xe2x80x94NHxe2x80x94CH3, xe2x80x94NHxe2x80x94C2H5, xe2x80x94NHxe2x80x94CH2xe2x80x94C2H5, xe2x80x94NHxe2x80x94CH(CH3)2, xe2x80x94NHxe2x80x94CH2CH2xe2x80x94C2H5, xe2x80x94NHxe2x80x94CH(CH3)xe2x80x94C2H5, xe2x80x94NHxe2x80x94CH2xe2x80x94CH(CH3)2 and xe2x80x94NHxe2x80x94C(CH3)3, preferably xe2x80x94NHxe2x80x94CH3 or xe2x80x94NHxe2x80x94C2H5, i.e., for example, CH2CH2xe2x80x94NHxe2x80x94CH3, CH2CH2xe2x80x94N(CH3)2, CH2CH2xe2x80x94NHxe2x80x94C2H5 or CH2CH2xe2x80x94N(C2H5)2;
C1-C4-alkylaminocarbonyl: COxe2x80x94NHxe2x80x94CH3, COxe2x80x94NHxe2x80x94C2H5, n-propylamino, COxe2x80x94NHxe2x80x94CH(CH3)2, COxe2x80x94NHxe2x80x94CH2CH2xe2x80x94C2H5, COxe2x80x94NHxe2x80x94CH(CH3)xe2x80x94C2H5, COxe2x80x94NHxe2x80x94CH2xe2x80x94CH(CH3)2 or COxe2x80x94NHxe2x80x94C(CH3)3, preferably COxe2x80x94NHxe2x80x94CH3 or COxe2x80x94NHxe2x80x94C2H5;
C1-C4-alkylaminocarbonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-alkylaminocarbonyl as mentioned above, preferably by COxe2x80x94NHxe2x80x94CH3 or COxe2x80x94NHxe2x80x94C2H5, i.e., for example, CH2xe2x80x94COxe2x80x94NHxe2x80x94CH3, CH2xe2x80x94COxe2x80x94NHxe2x80x94C2H5, CH2xe2x80x94COxe2x80x94NHxe2x80x94CH2xe2x80x94C2H5, CH2xe2x80x94COxe2x80x94NHxe2x80x94CH(CH3)2, CH2xe2x80x94COxe2x80x94NHxe2x80x94CH2CH2xe2x80x94C2H5, CH2xe2x80x94COxe2x80x94NHxe2x80x94CH(CH3)xe2x80x94C2H5, CH2xe2x80x94COxe2x80x94NHxe2x80x94CH2xe2x80x94CH(CH3)2, CH2xe2x80x94COxe2x80x94NHxe2x80x94C(CH3)3, CH(CH3)xe2x80x94COxe2x80x94NHxe2x80x94CH3, CH(CH3)xe2x80x94COxe2x80x94NHxe2x80x94C2H5, 2-(COxe2x80x94NHxe2x80x94CH3)ethyl, 2-(COxe2x80x94NHxe2x80x94C2H5)ethyl, 2-(COxe2x80x94NHxe2x80x94CH2xe2x80x94C2H5)-ethyl, 2-[CH2xe2x80x94COxe2x80x94NHxe2x80x94CH(CH3)2]ethyl, 2-(COxe2x80x94NHxe2x80x94CH2CH2xe2x80x94C2H5)ethy 2-[COxe2x80x94NHxe2x80x94CH(CH3)xe2x80x94C2H5]ethyl, 2-[COxe2x80x94NHxe2x80x94CH2xe2x80x94CH(CH3)2]ethyl, 2-[COxe2x80x94NHxe2x80x94C(CH3)3]ethyl, 2-(COxe2x80x94NHxe2x80x94CH3)propyl, 2-(COxe2x80x94NHxe2x80x94C2H5)propyl, 2-(COxe2x80x94NHxe2x80x94CH2xe2x80x94C2H5)propyl, 2-[CH2xe2x80x94COxe2x80x94NHxe2x80x94CH(CH3)2 ]propyl, 2-(COxe2x80x94NHxe2x80x94CH2CH2xe2x80x94C2H5)propyl, 2-[COxe2x80x94NHxe2x80x94CH(CH3)xe2x80x94C2H5]propyl, 2-[COxe2x80x94NHxe2x80x94CH2xe2x80x94CH(CH3)2]propyl, 2-[COxe2x80x94NHxe2x80x94C(CH3)3]propyl, 3-(COxe2x80x94NHxe2x80x94CH3)propyl, 3-(COxe2x80x94NHxe2x80x94C2H5)propyl, 3-(COxe2x80x94NHxe2x80x94CH2xe2x80x94C2H5)propyl, 3-[CH2xe2x80x94COxe2x80x94NHxe2x80x94CH(CH3)2]propyl, 3-(COxe2x80x94NHxe2x80x94CH2CH2xe2x80x94C2H5)propyl, 3-[COxe2x80x94NHxe2x80x94CH(CH3)xe2x80x94C2H5]propyl, 3-[COxe2x80x94NHxe2x80x94CH2xe2x80x94CH(CH3)2]propyl, 3-[COxe2x80x94NHxe2x80x94C(CH3)3]propyl, 2-(COxe2x80x94NHxe2x80x94CH3)butyl, 2-(COxe2x80x94NHxe2x80x94C2H5)-butyl, 2-(COxe2x80x94NHxe2x80x94CH2xe2x80x94C2H5)butyl, 2-[CH2xe2x80x94COxe2x80x94NHxe2x80x94CH (CH3)2]butyl, 2-(COxe2x80x94NHxe2x80x94CH2CH2xe2x80x94C2H5)butyl, 2-[COxe2x80x94NHxe2x80x94CH(CH3)xe2x80x94C2H5]butyl, 2-[COxe2x80x94NHxe2x80x94CH2xe2x80x94CH(CH3)2]butyl, 2-[COxe2x80x94NHxe2x80x94C(CH3)3]butyl, 3-(COxe2x80x94NHxe2x80x94CH3)butyl, 3-(COxe2x80x94NHxe2x80x94C2H5)butyl, 3-(COxe2x80x94NHxe2x80x94CH2xe2x80x94C2H5)-butyl, 3-[CH2xe2x80x94COxe2x80x94NHxe2x80x94CH(CH3)2]butyl, 3-(COxe2x80x94NHxe2x80x94CH2CH2xe2x80x94C2H5)butyl 3-[COxe2x80x94NHxe2x80x94CH(CH3)xe2x80x94C2H5]butyl, 3-[COxe2x80x94NHxe2x80x94CH2xe2x80x94CH(CH3)2]butyl, 3-[COxe2x80x94NHxe2x80x94C(CH3)3]butyl, 4-(COxe2x80x94NHxe2x80x94CH3)butyl, 4-(COxe2x80x94NHxe2x80x94C2H5)butyl, 4-(COxe2x80x94NHxe2x80x94CH2xe2x80x94C2H5)butyl, 4-[CH2xe2x80x94COxe2x80x94NHxe2x80x94CH(CH3)2]butyl, 4-(COxe2x80x94NHxe2x80x94CH2CH2xe2x80x94C2H5)butyl, 4-[COxe2x80x94NHxe2x80x94CH(CH3)xe2x80x94C2H5]butyl, 4-[COxe2x80x94NHxe2x80x94CH2xe2x80x94CH(CH3)2]butyl or 4-[COxe2x80x94NHxe2x80x94C(CH3)3]butyl, preferably CH2xe2x80x94COxe2x80x94NHxe2x80x94CH3, CH2xe2x80x94COxe2x80x94NHxe2x80x94C2H5, CH(CH3)xe2x80x94COxe2x80x94NHxe2x80x94CH3 or CH(CH3)xe2x80x94COxe2x80x94NHxe2x80x94C2H5;
di(C1-C4-alkyl)amino: N(CH3)2, N(C2H5)2, N,N-dipropylamino, N[CH(CH3)2]2, N(n-C4H9)2, N,N-Di-(1-methylpropyl)amino, N,N-di-(2-methylpropyl)amino, N[C(CH3)3]2, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methypropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethyl-ethyl)-N-(2-methylpropyl)amino, preferably N(CH3)2 or N(C2H5)2;
di(C1-C4-alkyl)amino-C1-C4-alkyl: C1-C4-alkyl which is substituted by di(C1-C4-alkyl)amino as mentioned above, i.e., for example, CH2N(CH3)2, CH2N(C2H5)2, N,N-dipropylaminomethyl, N,N-di[CH(CH3)2]aminomethyl, N,N-dibutylaminomethyl, N,N-di(1-methylpropyl)aminomethyl, N,N-di(2-methylpropyl)aminomethyl, N,N-di[C(CH3)3]aminomethyl, N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminomethyl, N-methyl-N-[CH(CH3)2]aminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N-(1-methylpropyl)aminomethyl, N-methyl-N-(2-methylpropyl)aminomethyl, Nxe2x80x94[C(CH3)3]xe2x80x94N-methylaminomethyl, N-ethyl-N-propylaminomethyl, N-ethyl-Nxe2x80x94[CH(CH3)2]aminomethyl, N-butyl-N-ethylaminomethyl, N-ethyl-N-(1-methylpropyl)aminomethyl, N-ethyl-N-(2-methylpropyl)aminomethyl, N-ethyl-Nxe2x80x94[C(CH3)3]-aminomethyl, Nxe2x80x94[CH(CH3)2]xe2x80x94N-propylaminomethyl, N-butyl-N-propylaminomethyl, N-(1-methylpropyl)-N-propylaminomethyl, N-(2-methylpropyl)-N-propylaminomethyl, Nxe2x80x94[C(CH3)3]xe2x80x94N-propylaminomethyl, N-butyl-N-(1-methylethyl)aminomethyl, Nxe2x80x94[CH(CH3)2]xe2x80x94N-(1-methylpropyl)aminomethyl, Nxe2x80x94[CH(CH3)2]xe2x80x94N-(2-methylpropyl)aminomethyl, Nxe2x80x94[C(CH3)3]xe2x80x94Nxe2x80x94[CH(CH3)2]aminomethyl, N-butyl-N-(1-methylpropyl)aminomethyl, N-butyl-N-(2-methylpropyl)aminomethyl, N-butyl-Nxe2x80x94[C(CH3)3]-aminomethyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminomethyl, Nxe2x80x94[C(CH3)3]xe2x80x94N-(1-methylpropyl)aminomethyl, Nxe2x80x94[C(CH3)3]xe2x80x94N-(2-methylpropyl)aminomethyl, N,N-dimethylaminoethyl, N,N-diethylaminoethyl, N,N-di(n-propyl)aminoethyl, N,N-di[CH(CH3)2]aminoethyl, N,N-dibutylaminoethyl, N,N-di(1-methylpropyl)aminoethyl, N,N-di(2-methylpropyl)aminoethyl, N,N-di[C(CH3)3]aminoethyl, N-ethyl-N-methylaminoethyl, N-methyl-N-propylaminoethyl, N-methyl-Nxe2x80x94[CH(CH3)2]aminoethyl, N-butyl-N-methylaminoethyl, N-methyl-N-(1-methylpropyl)aminoethyl, N-methyl-N-(2-methylpropyl)aminoethyl, Nxe2x80x94[C(CH3)3]xe2x80x94N-methylaminoethyl, N-ethyl-N-propylaminoethyl, N-ethyl-Nxe2x80x94[CH(CH3)2]aminoethyl, N-butyl-N-ethylaminoethyl, N-ethyl-N-(1-methylpropyl)aminoethyl, N-ethyl-N-(2-methylpropyl)aminoethyl, N-ethyl-Nxe2x80x94[C(CH3)3]aminoethyl, Nxe2x80x94[CH(CH3)2]xe2x80x94N-propylaminoethyl, N-butyl-N-propylaminoethyl, N-(1-methylpropyl)-N-propylaminoethyl, N-(2-methylpropyl)-N-propylaminoethyl, Nxe2x80x94[C(CH3)3]xe2x80x94N-propylaminoethyl, N-butyl-Nxe2x80x94[CH(CH3)2]aminoethyl, Nxe2x80x94[CH(CH3)2]xe2x80x94N-(1-methylpropyl)aminoethyl, Nxe2x80x94[CH(CH3)2]xe2x80x94N-(2-methylpropyl)aminoethyl, Nxe2x80x94[C(CH3)3]xe2x80x94Nxe2x80x94[CH(CH3)2]aminoethyl, N-butyl-N-(1-methylpropyl)aminoethyl, N-butyl-N-(2-methylpropyl)aminoethyl, N-butyl-Nxe2x80x94[C(CH3)3]aminoethyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminoethyl, Nxe2x80x94[C(CH3)3]xe2x80x94N-(1-methylpropyl)aminoethyl or Nxe2x80x94[C(CH3)3]xe2x80x94N-(2-methylpropyl)aminoethyl, in particular N,N-dimethylaminoethyl or N,N-diethylaminoethyl;
di(C1-C4-alkyl)aminocarbonyl: COxe2x80x94N(CH3)2, COxe2x80x94N(C2H5), COxe2x80x94N(CH2xe2x80x94C2H5)2, COxe2x80x94N[CH(CH3)2]2, COxe2x80x94N(n-C4H9)2, COxe2x80x94N[CH(CH3)xe2x80x94C2H5]2, COxe2x80x94N[CH2xe2x80x94CH(CH3)2]2, COxe2x80x94N[C(CH3)3]2, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-Nxe2x80x94[CH(CH3)2]aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl, Nxe2x80x94[C(CH3)3]xe2x80x94N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-Nxe2x80x94[CH(CH3)2]-aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl, N-ethyl-Nxe2x80x94[C(CH3)3]aminocarbonyl, Nxe2x80x94[CH(CH3)2]xe2x80x94N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, Nxe2x80x94[C(CH3)3]xe2x80x94N-propylaminocarbonyl, N-butyl-Nxe2x80x94[CH(CH3)2]aminocarbonyl, Nxe2x80x94[CH(CH3)2]xe2x80x94N-(1-methylpropyl)aminocarbonyl, Nxe2x80x94[CH(CH3)2]xe2x80x94N-(2-methylpropyl)aminocarbonyl, Nxe2x80x94[C(CH3)3]xe2x80x94Nxe2x80x94[CH(CH3)2]aminocarbonyl, N-butyl-N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl, N-butyl-Nxe2x80x94[C(CH3)3]aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl, Nxe2x80x94[C(CH3)3]xe2x80x94N-(1-methylpropyl)aminocarbonyl or Nxe2x80x94[C(CH3)3]xe2x80x94N-(2-methylpropyl)aminocarbonyl, preferably COxe2x80x94N(CH3)2 or COxe2x80x94N(C2H5)2;
di(C1-C4-alkyl)aminocarbonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by di(C1-C4-alkyl)aminocarbonyl as mentioned above, preferably by COxe2x80x94N(CH3)2 or COxe2x80x94N(C2H5)2, i.e., for example, CH2xe2x80x94COxe2x80x94N(CH3)2, CH2xe2x80x94COxe2x80x94N(C2H5)2, CH(CH3)xe2x80x94COxe2x80x94N(CH3)2 oder CH(CH3)xe2x80x94COxe2x80x94N(C2H5)2, preferably CH2xe2x80x94COxe2x80x94N(CH3)2 or CH(CH3)xe2x80x94COxe2x80x94N(CH3)2;
di(C1-C4-alkyl)phosphonyl: xe2x80x94PO(OCH3)2, xe2x80x94PO(OC2H5)2, N,N-dipropylphosphonyl, N,N-di-(1-methylethyl)phosphonyl, N,N-dibutylphosphonyl, N,N-Di-(1-methylpropyl)phosphonyl, N,N-di-(2-methylpropyl)phosphonyl, N,N-di-(1,1-dimethylethyl)phosphonyl, N-ethyl-N-methylphosphonyl, N-methyl-N-propylphosphonyl, N-methyl-N-(1-methylethyl)phosphonyl, N-butyl-N-methylphosphonyl, N-methyl-N-(1-methylpropyl)phosphonyl, N-methyl-N-(2-methylpropyl)phosphonyl, N-(1,1-dimethylethyl)-N-methylphosphonyl, N-ethyl-N-propylphosphonyl, N-ethyl-N-(1-methylethyl)phosphonyl, N-butyl-N-ethylphosphonyl, N-ethyl-N-(1-methylpropyl)phosphonyl, N-ethyl-N-(2-methylpropyl)phosphonyl, N-ethyl-N-(1,1-dimethylethyl)phosphonyl, N-(1-methylethyl)-N-propylphosphonyl, N-butyl-N-propylphosphonyl, N-(1-methylpropyl)-N-propylphosphonyl, N-(2-methylpropyl)-N-propylphosphonyl, N-(1,1-dimethylethyl)-N-propylphosphonyl, N-butyl-N-(1-methylethyl)phosphonyl, N-(1-methylethyl)-N-(1-methylpropyl)phosphonyl, N-(1-methylethyl)-N-(2-methylpropyl)phosphonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)phosphonyl, N-butyl-N-(1-methylpropyl)phosphonyl, N-butyl-N-(2-methylpropyl)phosphonyl, N-butyl-N-(1,1-dimethylethyl)phosphonyl, N-(1-methylpropyl)-N-(2-methylpropyl)phosphonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)phosphonyl or N-(1-dimethylethyl)-N-(2-methylpropyl)phosphonyl, preferably xe2x80x94PO(OCH3)2 or xe2x80x94PO(OC2H5)2;
di(C1-C4-alkyl)phosphonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by di(C1-C4-alkyl)phosphonyl as mentioned above, preferably by xe2x80x94PO(OCH3)2 or xe2x80x94PO(OC2H5)2, i.e., for example, CH2xe2x80x94PO(OCH3)2, CH2xe2x80x94PO(OC2H5)2, CH(CH3)xe2x80x94PO(OCH3)2 or CH(CH3)xe2x80x94PO(OC2H5)2;
C3-C6-alkenyl: prop-1-en-1-yl, allyl, 1-methylethenyl, 1-buten-1-yl, 1-buten-2-yl, 1-buten-3-yl, 2-buten-1-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex -5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl;
C3-C6-haloalkenyl: C3-C6-alkenyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;
cyano-C3-C6-alkenyl: for example 2-cyanoallyl, 3-cyanoallyl, 4-cyanobut-2-enyl, 4-cyanobut-3-enyl or 5-cyanopent-4-enyl;
C3-C6-alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl and 4-methylpent-2-yn-5-yl, preferably prop-2-yn-1-yl;
C3-C6-haloalkynyl: C3-C6-alkynyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 1,1-difluoroprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut -2-yn-1-yl, 5-fluoropent-3-yn-1-yl or 6-fluorohex-4-yn-1-yl;
cyano-C3-C6-alkynyl: for example 3-cyanopropargyl, 4-cyanobut-2-yn-1-yl, 5-cyanopent-3-yn-1-yl and 6-cyanohex-4-yn-1-yl;
C3-C4-alkenyloxy-C1-C4-alkyl: C1-C4-alkyl which is substituted by C3-C4-alkenyloxy such as allyloxy, but-1-en-3-yloxy, but-1-en-4-yloxy, but-2-en-1-yloxy, 1-methylprop-2-enyloxy or 2-methylprop-2-enyloxy, i.e., for example, allyloxymethyl, 2-allyloxyethyl or but-1-en-4-yloxymethyl, in particular 2-allyloxyethyl:
C3-C4-alkynyloxy-C1-C4-alkyl: C1-C4-alkyl which is substituted by C3-C4-alkynyloxy such as propargyloxy, but-1-yn-3-yloxy, but-1-yn-4-yloxy, but-2-yn-1-yloxy, 1-methylprop-2-ynyloxy or 2-methylprop-2-ynyloxy, preferably by propargyloxy, i.e., for example, propargyloxymethyl or 2-propargyloxymethyl, in particular 2-propargyloxymethyl;
(C3-C4-alkenyloxy)imino-C1-C4-alkyl: C1-C4-alkyl which is substituted by (C3-C4-alkenyloxy)imino such as allyloxyimino, but-1-en-3-yloxyimino, but-1-en-4-yloxyimino, but-2-en-1-yloxyimino, 1-methylprop-2-enyloxyimino or 2-methylprop-2-enyloxyimino, i.e., for example, allyloxy-Nxe2x95x90CHxe2x80x94CH2 or but-1-en-4-yloxy-Nxe2x95x90CH, in particular allyloxy-Nxe2x95x90CHxe2x80x94CH2;
C3-C4-alkenylthio-C1-C4-alkyl: C1-C4-alkyl which is substituted by C3-C4-alkenylthio such as allylthio, but-1-en-3-ylthio, but-1-en-4-ylthio, but-2-en-1-ylthio, 1-methylprop-2-enylthio or 2-methylprop-2-enylthio, i.e., for example, allylthiomethyl, 2-allylthioethyl or but-1-en-4-ylthiomethyl, in particular 2-(allylthio)ethyl;
C3-C4-alkynylthio-C1-C4-alkyl: C1-C4-alkyl which is substituted by C3-C4-alkynylthio such as propargylthio, but-1-yn-3-ylthio, but-1-yn-4-ylthio, but-2-yn-1-ylthio, 1-methylprop-2-ynylthio or 2-methylprop-2-ynylthio, preferably by propargylthio, i.e., for example, propargylthiomethyl or 2-propargylthioethyl, in particular 2-(propargylthio)ethyl;
C3-C4-alkenylsulfinyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by C3-C4-alkenylsulfinyl such as allylsulfinyl, but-1-en-3-ylsulfinyl, but-1-en-4-ylsulfinyl, but-2-en-1-ylsulfinyl, 1-methylprop-2-enylsulfinyl or 2-methylprop-2-enylsulfinyl, i.e., for example, allylsulfinylmethyl, 2-allylsulfinylethyl or but-1-en-4-ylsulfinylmethyl, in particular 2-(allylsulfinyl)ethyl;
C3-C4-alkynylsulfinyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by C3-C4-alkynylsulfinyl such as propargylsulfinyl, but-1-yn-3-ylsulfinyl, but-1-yn-4-ylsulfinyl, but-2-yn-1-ylsulfinyl, 1-methylprop-2-ynylsulfinyl or 2-methylprop-2-ynylsulfinyl, preferably propargylsulfinyl, i.e., for example, propargylsulfinylmethyl or 2-propargylsulfinylethyl, in particular 2-(propargylsulfinyl)ethyl;
C3-C4-alkenylsulfonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by C3-C4-alkenylsulfonyl such as allylsulfonyl, but-1-en-3-ylsulfonyl, but-1-en-4-ylsulfonyl, but-2-en-1-ylsulfonyl, 1-methylprop-2-enylsulfonyl or 2-methylprop-2-enylsulfonyl, i.e., for example, allylsulfonylmethyl, 2-allylsulfonylethyl or but-1-en-4-ylsulfonylmethyl, in particular 2-(allylsulfonyl)ethyl;
C3-C4-alkynylsulfonyl-C1-C4-alkyl; C1-C4-alkyl which is substituted by C3-C4-alkynylsulfonyl such as propargylsulfonyl, but-1-yn-3-ylsulfonyl, but-1-yn-4-ylsulfonyl, but-2-yn-1-ylsulfonyl, 1-methylprop-2-ynylsulfonyl or 2-methylprop-2-ynylsulfonyl, preferably by propargylsulfonyl, i.e., for example, propargylsulfonylmethyl or 2-propargylsulfonylethyl, in particular 2-(propargylsulfonyl)ethyl;
C3-C8-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;
C3-C8-cycloalkyl-C1-C6-alkyl: for example cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, 2-(cyclopropyl)ethyl, 2-(cyclobutyl)ethyl, 2-(cyclopentyl)ethyl, 2-(cyclohexyl)ethyl, 2-(cycloheptyl)ethyl, 2-(cyclooctyl)ethyl, 3-(cyclopropyl)propyl, 3-(cyclobutyl)propyl, 3-(cyclopentyl)propyl, 3-(cyclohexyl)propyl, 3-(cycloheptyl)propyl, 3-(cyclooctyl)propyl, 4-(cyclopropyl)butyl, 4-(cyclobutyl)butyl, 4-(cyclopentyl)butyl, 4-(cyclohexyl)butyl, 4-(cycloheptyl)butyl, 4-(cyclooctyl)butyl, 5-(cyclopropyl)pentyl, 5-(cyclobutyl)pentyl, 5-(cyclopentyl)pentyl, 5-(cyclohexyl)pentyl, 5-(cycloheptyl)pentyl, 5-(cyclooctyl)pentyl, 6-(cyclopropyl)hexyl, 6-(cyclobutyl)hexyl, 6-(cyclopentyl)hexyl, 6-(cyclohexyl)hexyl, 6-(cycloheptyl)hexyl or 6-(cyclooctyl)hexyl;
C3-C8-cycloalkyl, which contains a carbonyl or thiocarbonyl ring member: for example cyclobutanon-2-yl, cyclobutanon-3-yl, cyclopentanon-2-yl, cyclopentanon-3-yl, cyclohexanon-2-yl, cyclohexanon-4-yl, cycloheptanon-2-yl, cyclooctanon-2-yl, cyclobutanethion-2-yl, cyclobutanethion-3-yl, cyclopentanethion-2-yl, cyclopentanethion-3-yl, cyclohexanethion-2-yl, cyclohexanethion-4-yl, cycloheptanethion-2-yl or cyclooctanethion-2-yl, preferably cyclopentanon-2-yl or cyclohexanon-2-yl;
C3-C8-cycloalkyl-C1-C4-alkyl, which contains a carbonyl or thiocarbonyl ring member: for example cyclobutanon-2-ylmethyl, cyclobutanon-3-ylmethyl, cyclopentanon-2-ylmethyl, cyclopentanon-3-ylmethyl, cyclohexanon-2-ylmethyl, cyclohexanon-4-ylmethyl, cycloheptanon-2-ylmethyl, cyclooctanon-2-ylmethyl, cyclobutanethion-2-ylmethyl, cyclobutanethion-3-ylmethyl, cyclopentanethion-2-ylmethyl, cyclopentanethion-3-ylmethyl, cyclohexanethion-2-ylmethyl, cyclohexanethion-4-ylmethyl, cycloheptanethion-2-ylmethyl, cyclooctanethion-2-ylmethyl, 1-(cyclobutanon-2-yl)ethyl, 1-(cyclobutanon-3-yl)ethyl, 1-(cyclopentanon-2-yl)ethyl, 1-(cyclopentanon-3-yl)ethyl, 1-(cyclohexanon-2-yl)ethyl, 1-(cyclohexanon-4-yl)ethyl, 1-(cycloheptanon-2-yl)ethyl, 1-(cyclooctanon-2-yl)ethyl, 1-(cyclobutanethion-2-yl)ethyl, 1-(cyclobutanethion-3-yl)ethyl, 1-(cyclopentanethion-2-yl)ethyl, 1-(cyclopentanethion-3-yl)ethyl, 1-(cyclohexanethion-2-yl)ethyl, 1-(cyclohexanethion-4-yl)ethyl, 1-(cycloheptanethion-2-yl)ethyl, 1-(cyclooctanethion-2-yl)ethyl, 2-(cyclobutanon-2-yl)ethyl, 2-(cyclobutanon-3-yl)ethyl, 2-(cyclopentanon-2-yl)ethyl, 2-(cyclopentanon-3-yl)ethyl, 2-(cyclohexanon-2-yl)ethyl, 2-(cyclohexanon-4-yl)ethyl, 2-(cycloheptanon-2-yl)ethyl, 2-(cyclooctanon-2-yl)ethyl, 2-(cyclobutanethion-2-yl)ethyl, 2-(cyclobutanethion-3-yl)ethyl, 2-(cyclopentanethion-2-yl)ethyl, 2-(cyclopentanethion-3-yl)ethyl, 2-(cyclohexanethion-2-yl)ethyl, 2-(cyclohexanethion-4-yl)ethyl, 2-(cycloheptanethion-2-yl)ethyl, 2-(cyclooctanethion-2-yl)ethyl, 3-(cyclobutanon-2-yl)propyl, 3-(cyclobutanon-3-yl)propyl, 3-(cyclopentanon-2-yl)propyl, 3-(cyclopentanon-3-yl)propyl, 3-(cyclohexanon-2-yl)propyl, 3-(cyclohexanon-4-yl)propyl, 3-(cycloheptanon-2-yl)propyl, 3-(cyclooctanon-2-yl)propyl, 3-(cyclobutanethion-2-yl)propyl, 3-(cyclobutanethion-3-yl)propyl, 3-(cyclopentanethion-2-yl)propyl, 3-(cyclopentanethion-3-yl)propyl, 3-(cyclohexanethion-2-yl)propyl, 3-(cyclohexanethion-4-yl)propyl, 3-(cycloheptanethion-2-yl)propyl, 3-(cyclooctanethion-2-yl)propyl, 4-(cyclobutanon-2-yl)butyl, 4-(cyclobutanon-3-yl)butyl, 4-(cyclopentanon-2-yl)butyl, 4-(cyclopentanon-3-yl)butyl, 4-(cyclohexanon-2-yl)butyl, 4-(cyclohexanon-4-yl)butyl, 4-(cycloheptanon-2-yl)butyl, 4-(cyclooctanon-2-yl)butyl, 4-(cyclobutanethion-2-yl)butyl, 4-(cyclobutanethion-3-yl )butyl, 4-(cyclopentanethione-2-yl)butyl, 4-(cyclopentanethion-3-yl)butyl, 4-(cyclohexanethion-2-yl)butyl, 4-(cyclohexanethion-4-yl)butyl, 4-(cycloheptanethion-2-yl)butyl or 4-(cyclooctanethion-2-yl)butyl;
C3-C8-cycloalkyloxy-C1-C4-alkyl: cyclopropyloxymethyl, 1-cyclopropyloxyethyl, 2-cyclopropyloxyethyl, 1-cyclopropyloxyprop-1-yl, 2-cyclopropyloxyprop-1-yl, 3-cyclopropyloxyprop-1-yl, 1-cyclopropyloxybut-1-yl, 2-cyclopropyloxybut-1-yl, 3-cyclopropyloxybut-1-yl, 4-cyclopropyloxybut-1-yl, 1-cyclopropyloxybut-2-yl, 2-cyclopropyloxybut-2-yl, 3-cyclopropyloxybut-2-yl, 3-cyclopropyloxybut-2-yl, 4-cyclopropyloxybut-2-yl, 1-(cyclopropyloxymethyl)eth-1-yl, 1-(cyclopropyloxymethyl)-1-(cH3)-eth-1-yl, 1-(cyclopropylmethyloxy)prop-1-yl, cyclobutyloxymethyl, 1-cyclobutyloxyethyl, 2-cyclobutyloxyethyl, 1-cyclobutyloxyprop-1-yl, 2-cyclobutyloxyprop1-yl, 3-cyclobutyloxyprop-1-yl, 1-cyclobutyloxybut-1-yl, 2-cyclobutyloxybut-1-yl, 3-cyclobutyloxybut-1-yl, 4-cyclobutyloxybut-1-yl, 1-cyclobutyloxybut-2-yl, 2-cyclobutyloxybut-2-yl, 3-cyclobutyloxybut-2-yl, 3-cyclobutyloxybut-2-yl, 4-cyclobutyloxybut-2-yl, 1-(cyclobutyloxymethyl)eth-1-yl, 1-(cyclobutyloxymethyl)-1-(CH3)-eth-1-yl, 1-(cyclobutyloxymethyl)prop-1-yl, cyclopentyloxymethyl, 1-cyclopentyloxyethyl, 2-cyclopentyloxyethyl, 1-cyclopentyloxyprop-1-yl, 2-cyclopentyloxyprop-1-yl, 3-cyclopentyloxyprop-1-yl, 1-cyclopentyloxybut-1-yl, 2-cyclopentyloxybut-1-yl, 3-cyclopentyloxybut-1-yl, 4-cyclopentyloxybut-1-yl, 1-cyclopentyloxybut-2-yl, 2-cyclopentyloxybut-2-yl, 3-cyclopentyloxybut-2-yl, 3-cyclopentyloxybut-2-yl, 4-cyclopentyloxybut-2-yl, 1-(cyclopentyloxymethyl)eth-1-yl, 1-(cyclopentyloxymethyl)-1-(CH3)-eth-1-yl, 1-(cyclopentyloxymethyl)prop-1-yl, cyclohexyloxymethyl, 1-cyclohexyloxyethyl, 2-cyclohexyloxyethyl, 1-cyclohexyloxyprop-1-yl, 2-cyclohexyloxyprop-1-yl, 3-cyclohexyloxyprop-1-yl, 1-cyclohexyloxybut-1-yl, 2-cyclohexyloxybut-1-yl, 3-cyclohexyloxybut-1-yl, 4-cyclohexyloxybut-1-yl, 1-cyclohexyloxybut-2-yl, 2-cyclohexyloxybut-2-yl, 3-cyclohexyloxybut-2-yl, 3-cyclohexyloxybut-2-yl, 4-cyclohexyloxybut-2-yl, 1-(cyclohexyloxymethyl)eth-1-yl, 1-(cyclohexyloxymethyl)-1-(CH3)-eth-1-yl, 1-(cyclohexyloxymethyl)prop-1-yl, cycloheptyloxymethyl, 1-cycloheptyloxyethyl, 2-cycloheptyloxyethyl, 1-cycloheptyloxyprop-1-yl, 2-cycloheptyloxyprop-1-yl, 3-cycloheptyloxyprop-1-yl, 1-cycloheptyloxybut-1-yl, 2-cycloheptyloxybut-1-yl, 3-cycloheptyloxybut-1-yl, 4-cycloheptyloxybut-1-yl, 1-cycloheptyloxybut-2-yl, 2-cycloheptyloxybut-2-yl, 3-cycloheptyloxybut-2-yl, 3-cycloheptyloxybut-2-yl, 4-cycloheptyloxybut-2-yl, 1-(cycloheptyloxymethyl)eth-1-yl, 1-(cycloheptyloxymethyl)-1-(CH3)-eth-1-yl, 1-(cycloheptyloxymethyl)prop-1-yl, cyclooctyloxymethyl, 1-cyclooctyloxyethyl, 2-cyclooctyloxyethyl, 1-cyclooctyloxyprop-1-yl, 2-cyclooctyloxyprop-1-yl, 3-cyclooctyloxyprop-1-yl, 1-cyclooctyloxybut-1-yl, 2-cyclooctyloxybut-1-yl, 3-cyclooctyloxybut-1-yl, 4-cyclooctyloxybut-1-yl, 1-cyclooctyloxybut-2-yl, 2-cyclooctyloxybut-2-yl, 3-cyclooctyloxybut-2-yl, 3-cyclooctyloxybut-2-yl, 4-cyclooctyloxybut-2-yl, 1-(cyclooctyloxymethyl)-eth-1-yl, 1-(cyclooctyloxymethyl)-1-(CH3)-eth-1-yl or 1-(cyclooctyloxymethyl)prop-1-yl, in particular C3-C6-cycloalkoxymethyl or 2-(C3-C6-cycloalkoxy)ethyl.
3- to 7-membered heterocyclyl is a saturated, partially or fully unsaturated or aromatic heterocycle having from one to three heteroatoms selected from a group consisting of
one to three nitrogen atoms,
one or two oxygen and
one or two sulfur atoms.
Examples of saturated heterocycles which may contain a carbonyl or thiocarbonyl ring member are:
oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl, diaziridin-3-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl, 1,3-oxazolidin-3-yl, 1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, 1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl, tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydropyran-4-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, piperazin-3-yl, hexahydro-1,3,5-triazin-1-yl, hexahydro-1,3,5-triazin-2-yl, oxepan-2-yl, oxepan-3-yl, oxepan-4-yl, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl, 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl, 1,3-dioxepan-6-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,4-dioxepan-2-yl, 1,4-dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl, hexahydroazepin-3-yl, hexahydroazepin-4-yl, hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl, hexahydro-1,3-diazepin-4-yl, hexahydro-1,4-diazepin-1-yl und hexahydro-1,4-diazepin-2-yl.
Examples of unsaturated heterocycles which may contain a carbonyl or thiocarbonyl ring member are:
dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1,3-oxazolin-2-yl.
Preferred heteroaromatics are the 5-and 6-membered heteroaromatics, i.e., for example,
furyl, such as 2-furyl and 3-furyl, thienyl, such as 2-thienyl and 3-thienyl, pyrrolyl, such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl, such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl, such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl, such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl, such as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl, such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, imidazolyl, such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl, such as 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,3,4-oxadiazol-2-yl, thiadiazolyl, such as 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and 1,3,4-thiadiazol-2-yl, triazolyl, such as 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl, such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, such as 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl, such as 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in particular pyridyl, pyrimidyl, furanyl and thienyl.
All phenyl, carboxylic and heterocyclic rings are preferably unsubstituted or carry one substituent.
Preferred with a view to the use of the substituted (4-bromopyrazol-3-yl)benzazoles I as herbicides or desiccants/defoliants are those compounds I where the variables have the following meanings, in each case either on their own or in combination:
R1 is C1-C4-alkyl, in particular methyl;
R2 is C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-alkylsulfonyl, in particular C1-C4-haloalkoxy or C1-C4-alkylsulfonyl, particularly preferably difluoromethoxy;
R4 is hydrogen, fluorine or chlorine, in particular fluorine or chlorine;
R5 is cyano, halogen or trifluoromethyl, in particular halogen, particularly preferably chlorine;
A is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 or xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 which is attached to xcex1 via oxygen and sulfur, respectively, in particular xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the oxygen;
X is a chemical bond, oxygen, sulfur, xe2x80x94NHxe2x80x94 or xe2x80x94N(R7)xe2x80x94;
R6, R7 independently of one another are each C1-C6-alkyl, C1-C6-haloalkyl, cyano-C1-C4-alkyl, hydroxy-C1-C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, (C1-C4-alkoxy)carbonyl-C1-C4-alkyl, di(C1-C4-alkyl)aminocarbonyl-C1-C4-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl or phenyl-C1-C4-alkyl; if X is a chemical bond, oxygen, sulfur, xe2x80x94NHxe2x80x94 or xe2x80x94N(R7)xe2x80x94, R6 may also be (C1-C4-alkyl)carbonyl or C1-C4-alkylsulfonyl; if X is a chemical bond, R6 may furthermore be hydrogen, cyano, amino, halogen or xe2x80x94CHxe2x95x90CHxe2x80x94R8;
R6, R7 are in each case in particular C1-C6-alkyl, hydroxy-C1-C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or (C1-C4-alkoxy)carbonyl-C1-C4-alkyl; if X is a chemical bond, R6 may furthermore be in particular hydrogen or xe2x80x94CHxe2x95x90CHxe2x80x94R8;
R8 is (C1-C4-alkoxy)carbonyl.
Very particular preference is given to the substituted (4-bromopyrazol-3-yl)benzazoles of the formula Ia ({circumflex over (=)}I where R1=methyl, R2=difluoromethoxy, R4=hydrogen, R5=chlorine, Z=xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 which is attached to xcex1 via the sulfur), in particular to the compounds listed in Table 1 below:
Furthermore, particular preference is given to the substituted (4-bromopyrazol-3-yl)benzazoles of the formulae Ib to It and IA to IT, in particular to
the compounds Ib.001 to Ib.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R4 is chlorine: 
the compounds Ic.001 to Ic.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R4 is fluorine: 
the compounds Id.001 to Id.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is trifluoromethyl: 
the compounds Ie.001 to Ie.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is trifluoromethyl and R4 is chlorine: 
the compounds If.001 to If.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is trifluoromethyl and R4 is fluorine: 
the compounds Ig.001 to Ig.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is methylsulfonyl: 
the compounds Ih.001 to Ih.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is methylsulfonyl and R4 is chlorine: 
the compounds Ij.001 to Ij.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is methylsulfonyl and R4 is fluorine: 
the compounds Ik.001 to Ik.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the oxygen: 
the compounds Im.001 to Im.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R4 is chlorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the oxygen: 
the compounds In.001 to In.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R4 is fluorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the oxygen: 
the compounds Io.001 to Io.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is trifluoromethyl and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the oxygen: 
the compounds Ip.001 to Ip.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is trifluoromethyl and R4 is chlorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the oxygen: 
the compounds Iq.001 to Iq.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is trifluoromethyl and R4 is fluorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the oxygen: 
the compounds Ir.001 to Ir.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is methylsulfonyl and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the oxygen: 
the compounds Is.001 to Is.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is methylsulfonyl and R4 is chlorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the oxygen: 
the compounds It.001 to It.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is methylsulfonyl and R4 is fluorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the oxygen: 
the compounds IA.001 to IA.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that the group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 is attached to xcex1 via the nitrogen: 
the compounds IB.001 to IB.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R4 is chlorine and the group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 is attached to xcex1 via the nitrogen: 
the compounds IC.001 to IC.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R4 is fluorine and the group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 is attached to xcex1 via the nitrogen: 
the compounds ID.001 to ID.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is trifluoromethyl and the group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 is attached to xcex1 via the nitrogen: 
the compounds IE.001 to IE.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is trifluoromethyl and R4 is chlorine and the group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 is attached to xcex1 via the nitrogen: 
the compounds IF.001 to IF.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is trifluoromethyl and R4 is fluorine and the group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 is attached to xcex1 via the nitrogen: 
the compounds IG.001 to IG.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is methylsulfonyl and the group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 is attached to xcex1 via the nitrogen: 
the compounds IH.001 to IH.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is methylsulfonyl and R4 is chlorine and the group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 is attached to xcex1 via the nitrogen: 
the compounds IJ.001 to IJ.393, which differ from the corresponding compounds Ia.001 to Ia.393 only in that R2 is methylsulfonyl and R4 is fluorine and the group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 is attached to xcex1 via the nitrogen: 
the compounds IK.001 to IK.393, which differ from the corresponding compounds Ia.00 1 to Ia.393 only in that Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the nitrogen: 
the compounds IM.001 to IM.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R4 is chlorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the nitrogen: 
the compounds IN.001 to IN.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R4 is fluorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the nitrogen: 
the compounds IO.001 to IO.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is trifluoromethyl and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the nitrogen: 
the compounds IP.001 to IP.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is trifluoromethyl and R4 is chlorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the nitrogen: 
the compounds IQ.001 to IQ.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is trifluoromethyl and R4 is fluorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the nitrogen: 
the compounds IR.001 to IR.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is methylsulfonyl and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the nitrogen: 
the compounds IS.001 to IS.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is methylsulfonyl and R4 is chlorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the nitrogen: 
the compounds IT.001 to IT.393, which differ from the corresponding compounds Ia.001 to Ia.393 in that R2 is methylsulfonyl and R4 is fluorine and Z is a group xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Oxe2x80x94 which is attached to xcex1 via the nitrogen: 
The substituted (4-bromopyrazol-3-yl)benzazoles of the formula I can be obtained by various routes, in particular by one of the processes below:
A) Reaction of an aminophenylpyrazole of the formula IIIa or IIIb with a halogen and ammonium thiocyanate or with an alkali metal thiocyanate or alkaline earth metal thiocyanate: 
M⊕=alkali metal ion or 1/2 alkaline earth metal ion
The preferred halogen is chlorine or bromine; among the alkali metals/alkaline earth metal thiocyanates, preference is given to sodium thiocyanate.
In general, the reaction is carried out in an inert solvent/diluent, for example in a hydrocarbon, such as toluene and hexane, in a halogenated hydrocarbon, such as dichloromethane, in an ether, such as tetrahydrofuran, in an alcohol, such as ethanol, in a carboxylic acid, such as acetic acid, or in an aprotic solvent, such as dimethylformamide, acetonitrile and dimethyl sulfoxide.
The reaction temperature is usually between the melting point and the boiling point of the reaction mixture, preferably at from 0 to 150xc2x0 C.
To achieve as high a yield of the product of value as possible, halogen and ammonium thiocyanate or alkali metal/alkaline earth metal thiocyanate are employed in approximately equimolar amounts or in excess, up to about 5 times the molar amount, based on the amount of IIIa or IIIb.
A variant of the process entails reacting the aminophenylpyrazole IIIa or IIIb initially with ammonium thiocyanate or an alkali metal thiocyanate or alkaline earth metal thiocyanate to give a thiourea IVa or IVb 
and converting IVa or IVb subsequently into I where Z=xe2x80x94Nxe2x95x90C(XR6)xe2x80x94Sxe2x80x94 by treatment with halogen.
B) Diazotization of an aminophenylpyrazole of the formula IIIa or IIIb, conversion of the respective diazonium salt into an azidophenylpyrazole of the formula Va or Vb and its reaction either
B.1)with a carboxylic acid or
B.2)initially with a sulfonic acid (to give VIa or VIb), hydrolysis of the sulfonate formed to give aminophenol VIIa or VIIb, and its conversion into I: 
M⊕=alkali metal ion or 1/2 alkaline earth metal ion. 
For carrying out the diazotization, the details given for process C) apply. The conversion into the aryl azides Va/Vb is preferably carried out by reacting IIIa/IIIb with an alkali metal azide or alkaline earth metal azide such as sodium azide, or by reaction with trimethylsilyl azide.
The reaction with a carboxylic acid mentioned under B.1) is either carried out in an inert solvent, for example in an ether, such as tetrahydrofuran and dioxane, an aprotic solvent, such as dimethylformamide and acetonitrile, a hydrocarbon, such as toluene and hexane, a halogenated hydrocarbon, such as dichloromethane, or in the absence of a solvent in an excess of carboxylic acid R6xe2x80x94COOH. In the latter case, the addition of a mineral acid, such as phosphoric acid, may be advantageous. The reaction is preferably carried out at elevated temperature, for example at the boiling point of the reaction mixture. For the reaction of Va/Vb with a sulfonic acid Raxe2x80x94SO3H (where Ra is C1-C4-alkyl or C1-C4-haloalkyl, preferably methyl or trifluoromethyl) mentioned first under B.2), the details given above for the reaction of Va/Vb with R6xe2x80x94COOH apply. The subsequent hydrolysis of the sulfonates VIa/VIb is preferably carried out by reaction with an aqueous base, such as sodium hydroxide solution and potassium hydroxide solution, it being possible to add, if desired, a solvent, for example an ether, such as dioxane and tetrahydrofuran, or an alcohol, such as methanol and ethanol. The concluding reaction to give I is known per se and can be carried out in an extremely multifarious manner. In this context, reference is made to the details given in Houben-Weyl,
Methoden der Organischen Chemie, Georg Thieme Verlag Stuttgart, Vol. E8a 1993, p. 1032 ff.
The azidophenylpyrazoles of the formulae Va and Vb are new. Particularly preferred compounds of the formula Va are the compounds Va.1-Va.9 mentioned in Table 2 below:
C) Diazotization of substituted (4-bromopyrazol-3-yl)benzazoles of the formula I in which XR6 is amino, and subsequent conversion of the diazonium salt into compounds I where
xe2x80x94XR6=cyano or halogen {for the Sandmeyer reaction, cf., for example, Houben-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag Stuttgart, Vol. 5/4, 4th edition 1960, p. 438ff.},
xe2x80x94Xxe2x80x94=sulfur {cf., for example, Houben-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag Stuttgart, Vol.E11 1984, p. 43 and 176},
xe2x80x94XR6=for example xe2x80x94CH2xe2x80x94CH(halogen)-R8, xe2x80x94CHxe2x95x90CHxe2x80x94R8, xe2x80x94CHxe2x95x90C(halogen)-R8 {in general, these are products of a Meerwein arylation; cf., for example, C. S. Rondestredt, Org. React. 11, (1960), 189 and H. P. Doyle et al., J. Org. Chem. 42, (1977) 2431}: 
In general, the diazonium salt is obtained in a manner known per se by reacting I where xe2x80x94XR6=amino in an aqueous solution of an acid, for example in hydrochloric acid, hydrobromic acid or sulfuric acid, with a nitrite, such as sodium nitrite and potassium nitrite.
However, it is also possible to carry out the reaction in the absence of water, for example in hydrogen chloride-containing glacial acetic acid, in absolute alcohol, in dioxane or tetrahydrofuran, in acetonitrile or in acetone and to treat the starting material (I where xe2x80x94XR6=NH2) with a nitrous acid ester, such as tert-butyl nitrite and isopentyl nitrite.
The conversion of the diazonium salt obtained in this manner into the corresponding compound I where xe2x80x94XR6=cyano, chlorine, bromine or iodine is particularly preferably carried out by treatment with a solution or suspension of a copper(I) salt, such as copper(I) cyanide, copper(I) chloride, copper(I) bromide and copper(I) iodide, or with a solution of an alkali metal salt.
Compounds I where xe2x80x94Xxe2x80x94=sulfur are usually obtained by reacting the diazonium salt with a dialkyl disulfide, such as dimethyl disulfide and diethyl disulfide, or by using, for example, diallyl disulfide or dibenzyl disulfide.
The Meerwein arylation usually comprises the reaction of the diazonium salts with alkenes (here: H2Cxe2x95x90CHxe2x80x94R8) or alkynes (here: HCxe2x89xa1xe2x80x94Cxe2x80x94R8). Here, preference is given to employing an excess of the alkene or alkyne of up to about 3000 mol %, based on the amount of the diazonium salt.
The above-described reactions of the diazonium salt can be carried out, for example, in water, in aqueous hydrochloric acid or hydrobromic acid, in a ketone, such as acetone, diethyl ketone and methyl ethyl ketone, in a nitrile, such as acetonitrile, in an ether, such as dioxane and tetrahydrofuran, or in an alcohol, such as methanol and ethanol.
Unless stated otherwise for the individual reactions, the reaction temperatures are usually at from (xe2x88x9230) to +50xc2x0 C.
Preference is given to using all the reaction participants in approximately stoichiometric amounts; however, an excess of one the other component of up to about 3000 mol % may be advantageous.
D) Oxidation of a substituted (4-bromopyrazol-3-yl)benzazole I, in which X is sulfur to give I where X=xe2x80x94SOxe2x80x94 in a manner known per se (cf., for example, Houben-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag Stuttgart, Vol. E 11/1, 1985, p. 702 ff., Vol. IX, 4th edition, 1955, p. 211): 
Suitable oxidizing agents are, for example, hydrogen peroxide, organic peroxides, such as peracetic acid, trifluoroperacetic acid, m-chloroperbenzoic acid, tert-butyl hydroperoxide and tert-butyl hypochlorite, and also inorganic compounds, such as sodium metaiodate, chromic acid and nitric acid.
Depending on the oxidizing agent, the reaction is usually carried out in an organic acid, such as acetic acid and trichloroacetic acid, in a chlorinated hydrocarbon, such as methylene chloride, chloroform and 1,2-dichloroethane, in an aromatic hydrocarbon, such as benzene, chlorobenzene and toluene, or in a protic solvent, such as methanol and ethanol. Mixtures of the abovementioned solvents are also suitable.
The reaction temperature is generally at from (xe2x88x9230)xc2x0 C. to the boiling point of the reaction mixture in question, and preference is usually given to the lower temperature range. Advantageously, starting material and oxidizing agent are employed in an approximately stoichiometric ratio; however, it is also possible to employ an excess of one or the other component.
E) Oxidation of a substituted (4-bromopyrazol-3-yl)benzazole I, where X is sulfur or xe2x80x94SOxe2x80x94, to give I where X=xe2x80x94SO2xe2x80x94 in a manner known per se (cf., for example, Houben-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag Stuttgart, Vol. E 11/2, 1985, p. 1132 ff. and Vol. IX, 4th edition, 1955, p. 222 ff.): 
Suitable oxidizing agents are, for example, hydrogen peroxide, organic peroxides, such as peracetic acid, trifluoroperacetic acid and m-chloroperbenzoic acid, furthermore inorganic oxidizing agents, such as potassium permanganate. The presence of a catalyst, for example tungstate, can have advantageous effects on the course of the reaction.
In general, the reaction is carried out in an inert solvent; suitable solvents being, depending on the oxidizing agent, for example organic acids, such as acetic acid and propionic acid, chlorinated hydrocarbons, such as methylene chloride, chloroform and 1,2-dichloroethane, aromatic hydrocarbons or halogenated hydrocarbons, such as benzene, chlorobenzene and toluene, or water. It is also possible to use mixtures of the abovementioned solvents.
Usually, the reaction is carried out at from (xe2x88x9230)xc2x0 C. to the boiling point of the reaction mixture in question, preferably at from 10xc2x0 C. to the boiling point.
Advantageously, the starting material I where X=sulfur or SO and the oxidizing agent are employed in approximately stoichiometric amounts. However, to optimize the conversion of the starting material, it may be advisable to employ an excess of oxidizing agent.
F) Reaction of a substituted (4-bromopyrazol-3-yl)benzazole I where the grouping xe2x80x94XR6 is chlorine, bromine, alkylsulfonyl or haloalkylsulfonyl in the presence of a base with an alcohol, mercaptan, amine or a CH-acidic compound (VIII): 
Rb and Rc independently of one another are each cyano or (C1-C4-alkoxy)carbonyl.
Advantageously, the reaction is carried out in an inert solvent, for example in an ether, such as diethyl ether, methyl tert-butyl ether, dimethoxy ethane, diethylene glycol dimethyl ether, tetrahydrofuran and dioxane, a ketone, such as acetone, diethyl ketone, ethyl methyl ketone and cyclohexanone, a dioplar aprotic solvent, such as acetonitrile, dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, a protic solvent such as methanol and ethanol, an aromatic, if desired halogenated, hydrocarbon, such as benzene, chlorobenzene and 1,2-dichlorobenzene, a heteroaromatic solvent, such as pyridine and quinoline, or in a mixture of such solvents. Tetrahydrofuran, acetone, diethyl ketone and dimethylformamide are preferred.
Suitable bases are, for example, the hydroxides, hydrides, alkoxides, carbonates or bicarbonates of alkali metal and alkaline earth metal cations, tertiary aliphatic amines, such as triethylamine, N-methylmorpholine and N-ethyl-N,N-diisopropylamine, bi- and tricyclic amines, such as diazabicycloundecane (DBU) and diazabicyclooctane (DABCO), or aromatic nitrogen bases, such as pyridine, 4-dimethylaminopyridine and quinoline. Combinations of different bases are also suitable. Preferred bases are sodium hydride, sodium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide and potassium tert-butoxide.
The amines H2NR6 or HN(R6)R7 may serve as reaction participants and simultaneously as bases, in which case the amine should be present in at least a two-fold excess, based on the amount of the starting material I. It is, of course, also possible to employ a greater excess of amine, up to approximately 10 times the molar amount, based on the amount of I where xe2x80x94XR6=Cl, Br, xe2x80x94SO2-alkyl or xe2x80x94SO2-haloalkyl.
The starting materials are generally employed in approximately stoichiometric amounts; however, an excess of one or the other components may be advantageous with a view to the practice of the process or to obtain as complete a conversion of the starting material I {xe2x80x94XR6≈Cl, Br, xe2x80x94SO2-alkyl, xe2x80x94SO2-haloalkyl} as possible.
The molar ratio of alcohol, mercaptan, amine or CH-acidic compound (VIII) to base is generally from 1:1 to 1:3.
The concentration of the starting materials in the solvent is usually at from 0.1 to 5.0 mol/l.
The reaction can be carried out at temperatures of from 0xc2x0 C. to the reflux temperature of the reaction mixture in question.
G) Reaction of a substituted (4-bromopyrazol-3-yl)benzazole I in which xe2x80x94XR6 is halogen with a (C1-C6-alkyl)-Grignard reagent: 
Here, Hal is chloride or bromide.
In general, the reaction is carried out in an inert solvent/diluent, for example a hydrocarbon, such as hexane or toluene, or an ether, such as diethyl ether, tetrahydrofuran and dioxane.
If desired, it is possible to add a transition metal catalyst in amounts of from 0.0001 to 10 mol %. Suitable transition metal catalysts are, for example, nickel and palladium catalysts, such as nickel dichloride, bis(triphenylphosphine)nickel dichloride, [bis(1,2-diphenylphosphino)ethane]nickel dichloride, [bis(1,3-diphenylphosphino)propane]nickel dichloride, palladium dichloride, tetrakis(triphenylphosphine)-palladium, bis(triphenylphosphine)palladium dichloroide, [bis(1,2-diphenylphosphino)ethane]palladium dichloride, [bis(1,3-diphenylphosphino)propane]palladium dichloride and [bis(diphenylphosphino)ferrocene]palladium dichloride, but also mixtures of palladium dichloride or nickel dichloride and phosphines, such as triphenylphosphine, bis-1,2-(diphenylphosphino)ethane and bis-1,3-(diphenylphosphino)propane. Depending on the practice of the reaction, this gives rise to compounds I where xe2x80x94XR6=hydrogen or C1-C6-alkyl or to corresponding compounds of alkylated and non-alkylated compound I which can, however, be separated in a customary manner.
In general, the reaction is carried out at from (xe2x88x92100)xc2x0 C. to the boiling point of the reaction mixture.
The amount of Grignard reagent is not critical; usually, (C1-C6-alkyl)-MgHal is employed in an approximately equimolar amount or in excess, up to about 10 times the molar amount, based on the amount of I where xe2x80x94XR6=halogen.
Unless stated otherwise, all the processes described above are advantageously carried out under atmospheric pressure or under the autogenous pressure of the reaction mixture in question.
The work-up of the reaction mixtures is usually carried out in a conventional manner. Unless stated otherwise in the processes described above, the products of value are obtained, for example, after the dilution of the reaction solution with water by filtration, crystallization or solvent extraction, or by removing the solvent, partitioning the residue in a mixture of water and a suitable organic solvent and work-up of the organic phase to afford the product.
The substituted (4-bromopyrazol-3-yl)benzazoles I can be obtained as isomer mixtures in the preparation; however, if desired, these can be separated into largely pure isomers using customary methods such as crystallization or chromatography, including chromatography over an optically active adsorbate. Pure optically active isomers can be prepared advantageously from suitable optically active starting materials.
Agriculturally useful salts of the compounds I can be formed by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reaction with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
Salts of I where the metal ion is not an alkali metal ion can be prepared by cation exchange of the corresponding alkali metal salt in a conventional manner, similarly ammonium, phosphonium, sulfonium and sulfoxonium salts by means of ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
The compounds I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
Taking into account the universality of the application methods, the compounds I, or herbicidal compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays. 
In addition, the compounds I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.
Moreover, the substituted (4-bromopyrazol-3-yl)benzazoles I are also suitable for the desiccation and/or defoliation of plants.
As desiccants, they are suitable, in particular, for desiccating the aerial parts of crop plants such as potatoes, oilseed rape, sunflowers and soybeans. This allows completely mechanical harvesting of these important crop plants.
It is also of economic interest to facilitate harvesting, which is made possible by concentrating, over a period of time, dehiscence, or reducing the adherence to the tree, in citrus fruit, olives or other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. promotion of the formation of abscission tissue between fruit or leaf and shoot of the plants, is also important for readily controllable defoliation of useful plants, in particular cotton.
Moreover, shortening the period within which the individual cotton plants mature results in improved fiber quality after harvesting.
The compounds I, or the compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend on the intended aims; in any case, they should guarantee the finest possible distribution of the active compounds according to the invention.
Suitable inert auxiliaries are essentially: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and water.
Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the substances, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.
Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.
Powders, materials for spreading and dusts can be prepared by mixing or grinding the active compounds together with a solid carrier.
Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
The concentrations of the active compounds I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise approximately from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds I are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
The formulation examples which follow illustrate the preparation of such products:
I. 20 parts by weight of the compound No. In.003 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
II. 20 parts by weight of the compound No. Im.003 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to I mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
III. 20 parts by weight of the active compound No. Ik.003 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280xc2x0 C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to I mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
IV. 20 parts by weight of the active compound No. It.003 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-xcex1-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active compound.
V. 3 parts by weight of the active compound No. In.003 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of active compound.
VI. 20 parts by weight of the active compound No. Im.003 are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.
VII. 1 part by weight of the compound No. Ik.003 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. The mixture can then be diluted with water to the desired concentration of active compound. This gives a stable emulsion concentrate.
VIII. 1 part by weight of the compound No. It.003 is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol(copyright) EM 31 (=nonionic emulsifier based on ethoxylated castor oil from BASF). The mixture can then be diluted with water to the desired concentration of active compound. This gives a stable emulsion concentrate.
The active compounds I or the herbicidal compositions can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into as little contact as possible, if any, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
The rates of application of active compound I are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.
To widen the spectrum of action and to achieve synergistic effects, the substituted (4-bromopyrazol-3-yl)benzazoles I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compounds and then applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryl/hetaryl-oxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetaryl aryl ketones, benzyl-isoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivates, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.
It may furthermore be advantageous to apply the compounds I, alone or in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.